Azodyestuffs insoluble in water and process of making same



Patented Feb. 23, 1932 UNITED STATES PATENT OFFICE ABTEUB zrrscnnn, or OFFENBACHLON-THE-MAIN, Ann nonnnr'scnmr'rf or DARMSTADT, GERMANY, ASSIGNOBS TO GENERAL ANILINE WORKS) INC., OF NEW w: I

YORK, N. Y., A CORPORATION OF DELAWARE 1 AZODYESTUIFS msorunnn m WATER AND ritocnss on MAKINGl seam No Drawing. Application filed April 3, 1929, Serial No. 352,317, and in Germenylpril 7, 1928.

E r Hem/ts wherein R means a diaryl residue which may contain further substituents. Especially 20 suitable for our process are those dihydroxy quinoline compounds which contain a diaryl residue of the diphenyl series. The dihydroxy quinoline compounds used in our process may be prepared, for example, in an analogous manner as described in Berichte der Deutschen Chemischen Gesellschaft, v01. 60, page 832 or 1108.

Whereas QA-dihydroxy quinoline itself yields useless dyeings when employed for the manufacture of ice-colors, according to our process valuable pigment dyestuils are obtained by means of the usual substrate, or fast dyeings and printings on the fiber by producing the dyestufis according to the icecolor method. In consequence of the substantive properties of the combining components the goods padded therewithmay be developed without being previously dried.

In order to further illustrate our invention the following examples are given, all temperatures being in centigrade degrees but it may be understood that our invention is not limited to the particular products or conditions of reaction mentioned therein.

Example Cotton yarn previouslytreatedwin a suit able manner is impregnated withwa solution containing per. liter 3.5 grs, of 2.4 2 4:

prepared from benzidine and malonic ester in an analogous manner as described in Berichte der Deutsohen Chemischen Gesellschaft, vol. 60, page 1108, 5.5 com. of a caustic soda solution of 34 B., 3.5 com. of Turkey red oil and 28 grs. of Glaubers salt. Then it is wrung out and developed in the presence of acetic acid with a solution containing per liter :1 hundredth molecular proportion of diazotized l-amino-anthraquinone.

In this manner a brownish red-orange dyeing of a very good fastness is obtained.

The following table shows the shades of dyeings prepared in the same way from the same padding solution and from the diazo compounds of the following bases:

Base Shade -a1nino-diphenyI-ether. .fi-dichloro-aniline. -nitro-2.amino-to1uene. amino-azmtoluene.

Orange-yellow. Brownish-orange. Brownlsh'orange. yellowish-red.

diazotized compound of the benzene or anthracene series not containing sulfonic or carboxylic groups with 2.4-24'-tetrahydroxy- 5 6.6l-diquinolyl of the probable general for- OH on t t Hi MB v no-ekbrmN o-on 2. As new compounds the azo dyestufls of the probable general formula on on wherein the Xs mean aryl residues of the benzene or anthracene series, which compounds arecolored powders, insoluble 1n water, y1eld1ng valuable color lakes or when pro- 7 duced on the-fiber fast dyeings and printings.

In testimony whereof I aflix my signature.

' ARTHUR ZITSOHER. In testimony whereof I afllx my si ature.

ROBERT SCHMI T. 

